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Tuscany self guided cycling holiday

country:Italy
location:Tuscany 
trip type:Self guided, moderate cycling holidays
departures:This trip can start any day between 15th March and the end of October
price:From €1120 (7 days) excluding flights and bike hire. Price based on double occupancy. Includes accommodation in 3-star properties, breakfasts, route notes, luggage transfers and assistance if necessary
vouchers:Gift vouchers can be used with this holiday

introduction to Tuscany self guided cycling holiday

Tuscany and beauty go hand in hand. Tuscan landscape, architecture, wine, food. All are beautiful and inspiring. This is where Michelangelo and Leonardo da Vinci created their best works of art! These you will discover and more during the course of this week-long cycling tour.

This tour will take you from medieval Pienza to Certaldo where you can board a train to Florence. In between, you’ll ride through and by countless remarkable sites; no less than 5 of them (Pienza, Val d’Orcia, Siena, San Gimignano, and Florence) have been deemed so exceptional that they are listed as UNESCO World Heritage Sites. Rides take place on rolling terrain with some steep hills. To be fully enjoyed, this trip requires a fairly good condition.

Trip highlights:
  • Cycling through lofty hill towns, broad valleys and sinuous country roads past cypress-lined lanes and quiet woodland.
  • Visits of the magnificent cities of Pienza, Siena and San Gimignano.
  • Visit of the remote convent where parts of The English Patient were filmed, the town of Montepulciano, home to the famous Vino Nobile di Montepulciano, the antique thermal spa of Bagno Vignoni and the famed Monte Oliveto Maggiore monastery.
Also possible: Car transfer from Florence to Pienza upon your arrival; train from Certaldo to Florence or car transfer from San Gimignano to Florence before your departure; shopping at a first-class ceramics workshop in Castello di Brolio; wine-tasting at the fortress of Castello di Brolio; short route to Certaldo.
day-by-day itinerary
Day 1:Arrival in Pienza. Arrive in Pienza. Please note that the closest station to Pienza is Chiusi—35 km from Pienza--on the Rome-Florence train line. Alternatively, we can arrange a car transfer from Florence to Pienza. After checking-in at your pre-arranged charming hotel, you’ll meet our local representative who will outfit you with bikes and meticulously go over the itinerary. Pienza is one of the four UNESCO World Heritage Sites you’ll encounter during your week-long history-laden cycling trip.
Day 2:Loop from Pienza to Pienza through Montepulciano - 50 km (31 miles). You’ll follow a route that winds through a scenic landscape checkered with vineyards, cypresses, and medieval villages…This where the English Patient was filmed. Among the sites you’ll ride through is the hilltop village of Castelmuzio and Montepulciano, another hilltop village that will make a perfect lunch/wine stop (Montepulciano is home to the famous Vino Nobile di Montepulciano) before heading back to Pienza through Monticchiello, another hilltop village!
Day 3:Pienza to Montalcino - 46 km (29 miles). Today’s ride will take you to Bagno Vignoni, a thermal spa town that dates back to Roman times, before reaching the beautiful Castiglione d'Orcia. The monastery of Sant'Antimo is your next stop—with luck, you will hear the monks chanting. Montalcino is your destination where wine shopping for the famous local Brunello is a must.
Day 4:Montalcino to Siena - 60 km (37.5 miles). Your detailed directions will take you through typical postcard Tuscan scenery, Italy’s most photographed region—for good reason. Following a picturesque crest road, you’ll ride by the Monte Oliveto Maggiore monastery—which also makes a nice lunch spot before cycling on to Siena, your final destination. Make the best of your afternoon and explore its countless treasures such as its unfinished Duomo and its famous Piazza del Campo where twice a year the disputed “Palio” horse race is held opposing the 17 “contrade” of this fascinating city.
Day 5:Siena to Castellina-in-Chianti – 45 km (or 28 miles). Another day of hill climbing with many recovery sites on your way including medieval Castelnuovo Berardenga, the gateway town to the Chianti wine-producing region. A bit further is the impressive fortress of Castello di Brolio where a wine-tasting can be done. Your destination is Castellina in Chianti.
Day 6:Castellina to San Gimignano - 60 km (37.5 miles). On your way, you’ll ride through the walled town of Monteriggioni that offers views in the distance of San Gimignano—your final destination—and its distinctive skyline of stone towers. San Gimignano is exceptional (it is a UNESCO World Heritage site) and we cannot recommend enough an early arrival to discover this fascinating place. This lively city houses a number of exceptional restaurants set in historic buildings that will contribute to making your gastronomic experience a memorable one.
Day 7:Departure (Certaldo). After breakfast, depart San Gimignano at the time of your choice. Note that you may also opt to ride a short route that will take you to Certaldo (worth a visit) where you’ll hop on a train to Florence (a 50 minutes’ ride). Alternatively, we can arrange a car transfer from San Gimignano to Florence.
how this holiday makes a difference
We offer you a unique way to offset your carbon by using pollution-free bicycles. Travelling by bike, you are no longer an observer you are a peaceful and friendly actor of local people, environment and culture.

Travelling on small and quiet roads, this tour will allow you to experience part of the rural countryside and ride through famous and not-so-famous small and authentic villages that all so well illustrate the multi-faceted Tuscan character.

This tour will give you plenty of opportunities to enjoy the farming activity of the region. Chianti lands are rich with patchwork of wines and olive trees standing out in orderly rows against the hills tamed by the farmers' skill. The Sienese Crete extends in an area which stretches from Siena to Montepulciano. With the ending of the lease farming system, pastoral farming has taken over, and therefore, the farms in this area now produce excellent quality pecorino cheese, milk and specialise in the gathering of white truffles and the cultivation of olives.

Relying on local guides and family-owned hotels, you will be ensured a warm, personalized welcome. All properties are run by people who have a passion for their region and its cultural, gastronomic, and historical heritage. We use genuine places with local charm, blending harmoniously into the environment. Our hotels offer guests a pleasant, nice-sized environment. Some of them have as few as two rooms, while others are small human-sized hotels.

We are based in France. This is where we live and work. Our office is located in the French Alps, just a stones throw from the Swiss border, and we ride the very same roads we recommend to you for your cycling vacations. As firm believers of sustainable development, we have established a friendly network of professionals, comprised mainly of local tour guides, small operators, and family-run agencies. Most of our people have created their own jobs/enterprises in order to live their passion for the region and cultural heritage. All have extensive travel experience and have lived in various places before falling in love with the area they now call home.

Traveling with us guarantees that you will be taken care of by caring professionals who chose to build their lives here. Forget the non-descript and indistinguishable big chain hotels; we use genuine places with local charm. All the properties we use are run by people who have a passion for their region and its cultural, gastronomic, and historical heritage.'

We recommend travel by train, a much more eco-friendly solution. To travel within Europe, we recommend taking trains over renting cars, or air transports. Trains are more energy-efficient and will minimize the CO2 emission by capita. When flying is required, prefer an airline that contributes to funds aimed at offsetting carbon emissions.

In cities, we recommend clients to use public transportations, or to walk or bike. City bike rentals are more and more widely available in big and medium-sized cities across Europe they are the best way to get around congested cities. Our travel tips include a list of renters.

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